12 Questions We Wish We Could Ask On A First Date

Some questions can give you a good gauge of character. But these are sometimes also the questions that we shouldn’t ask on a first date… if we want there to be a second date, that is.

Are we going to do the ‘X amount of dates before we sleep together’ thing?

There are only two things that you may come off as – prudish or skanky. So as much as you want to know, hit mute on the question and just vibe it out to see how things go.

What are your thoughts on shaving/not shaving?

It’s a legitimate concern for both parties. But the same as how you don’t want to think about his hairy untamed underarms, legs and nether regions, he doesn’t want to think of yours either. You might both be okay with a little hair here and there, but first dates are not a time to clarify that.

Are you in this for fun or do you think this is going somewhere?

Obviously, we all want to be going somewhere with this, but sometimes we just want to have a little fun. Asking straight up would be in bad taste, so again, vibe it out and see how things go.

Are we still going to be able to have our own lives?

Some people are obnoxiously dependent and it’s nice to know what you’re getting into before you’re in too deep. But forthcoming-ness might not be the best way to find out if they’re horribly clingy.

How much do you actually make?

Sure, it’s a pertinent question. How much he earns often dictates his lifestyle. But he’s only going to see the words “GOLD DIGGER” stamped on your forehead it you talk about finances so soon.

How often do you watch porn?

You could ask, but there is a high possibility that he’s going to lie anyway, so broach the subject at a later time if it’s really such an issue.

Are you seeing (or sleeping with) other people?

It’s another legitimate question, especially if the first date is going to lead to a second and a third and a fourth. But you run the risk of seeming overeager or too possessive too soon. Easy does it, sweetheart, easy does it.

What’s your ‘number’?

Inquiring about their past sexual partners is not going to go over well. It’s important to know whether they’ve been around the block (because it tells you their views of life and love and sex), but it’s a little too personal for a first date.

Why are you still single?

It’s kind of a compliment because it implies that he’s too good to be true, but at the same time you really want to dig deeper to see if he has any flaws. He’ll just squirm in his seat, wondering whether to laugh or to try to make you laugh by bringing up an embarrassing flaw.

Are you still friends with your ex?

Knowing if he’s on good terms with his ex tells you a lot about his maturity and how he views and handles the relationships in his life. But he’ll be thinking that it’s the first date, and you’re already possessive about exes.

Have you ever cheated on someone?

Yes, you want to know if you can trust them. Nothing is worse than finding out you’re dating a rat. But not unlike asking about their porn consumption, guys almost never come clean about their indiscretions.